The use of perfluoroalkyl—(in the following abbreviated as RF) substituted polymers to impart oil and water repellency to a variety of substrates such as textiles and paper is well known. The vast majority of these polymers are perfluoroalkyl-substituted acrylate copolymers useful for treating paper and paper products to impart oil and water repellency. U.S. Pat. No. 3,919,183 (Jager et al.) discloses polymers useful as oil repellant coatings for porous substrates such as textile materials and paper which comprise a perfluoroalkylethyl acrylate. U.S. Pat. No. 4,582,882 (Lynn et al.) describes fluorinated paper sizes which are copolymers of perfluoroalkyl acrylate. Also U.S. Pat. No. 5,674,961 of Fitzgerald discloses fluorochemical polymers useful for water, oil and grease resistance to paper. The monomers used to synthesize the above perfluoroalkylated polymers are derived exclusively from RF-substituted alcohols where an ethylene group is present between the RF and the hydroxyl group.
Several patents also describe RF-substituted polyurethanes, for example U.S. Pat. No. 5,663,273. Polyamide-amino polymers derived from polyethyleneimine by reaction with esters of perfluoroalkyl-substituted carboxylic acids are described in U.S. Pat. Nos. 3,769,307 and 3,567,500. These polymers contain a mixture of RF-substituted amide and secondary amino groups. These polymers are used to impart oleophobicity yet hydrophilicity to textile substrates.
Di-RF amidomonocarboxylic acids prepared from 1 equivalent of diethylenetriamine, 2 equivalents of an RF-acid and 1 equivalent of an anhydride are taught for use as textile finishes in U.S. Pat. No. 3,754,026. Similar RF-amide-substituted polyethyleneimines useful as chemically resistant surfactants are described in U.S. Pat. No. 3,271,430. They are obtained by reaction of a perfluorinated alkanoic acid with a large excess of ethyleneimine. Reaction products of RF-substituted acids with polymers bearing pendent primary amino groups attached to a carbon-carbon backbone by a linking group are claimed in U.S. Pat. No. 4,606,973 as low surface energy coatings for flat substrates.
U.S. Pat. No. 3,818,074 describes saturated and unsaturated fluorinated alcohols which can have 2 to 12 methylene groups separating a perfluoroalkyl radical having from three to 12 carbon atoms and the hydroxyl group.
U.S. Pat. No. 3,498,958, discloses perfluoroalkyl amidoalkyl alcohols which have 1 to 14 methylene groups separating the perfluoroalkyl radical and the amido group, (meth)acrylate esters thereof and copolymers derived therefrom. The amidoalkyl alcohols are the saturated analogues of the amidoalkanols of formula I described below, and are obtained by a different synthetic route.